US2025204243A1PendingUtilityA1
Heterocyclic compound, organic light emitting device comprising the same and composition for organic material layer
Est. expiryDec 15, 2043(~17.4 yrs left)· nominal 20-yr term from priority
H10K 2101/90C09K 11/06H10K 50/11H10K 50/181H10K 50/15H10K 85/6576H10K 85/654H10K 85/6572H10K 85/6574H10K 85/636C07D 405/12C07D 405/04C07D 409/14C07D 405/14H10K 85/615H10K 85/633H10K 2101/10
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Claims
Abstract
The present disclosure relates to a heterocyclic compound represented by Chemical Formula 1, an organic light emitting device including the same, and a composition for an organic material layer.
Claims
exact text as granted — not AI-modified1 . A heterocyclic compound represented by the following Chemical Formula
wherein, in Chemical Formula 1,
R1 to R10 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; Ar1; —P(═O)R101R102; —SiR101R102R103; and the following Chemical Formula 2, or two or more groups adjacent to each other bond to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C60 heteroring, and R101, R102 and R103 are the same as or different from each other and each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group;
any one of R1 to R10 is the following Chemical Formula 2, and another one is Ar1; and
Ar1 is a substituted or unsubstituted C6 to C60 aryl group; or the following Chemical Formula 3,
in Chemical Formula 2,
L1 to L3 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group;
a is an integer of 0 to 5, and when a is 2 or greater, L1s are the same as or different from each other;
b is an integer of 0 to 5, and when b is 2 or greater, L2s are the same as or different from each other;
c is an integer of 0 to 5, and when c is 2 or greater, L3s are the same as or different from each other;
Ar2 and Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C60 aryl group; or the following Chemical Formula 3; and
any one of Ar1 to Ar3 is the following Chemical Formula 3,
in Chemical Formula 3,
R11 and R12 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; —P(═O)R101R102; —SiR101R102R103; and —NR101R102, or two or more groups adjacent to each other bond to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C60 heteroring, and R101, R102 and R103 are the same as or different from each other and each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group;
d is an integer of 0 to 3, and when d is 2 or greater, R11s are the same as or different from each other;
e is an integer of 0 to 4, and when e is 2 or greater, R12s are the same as or different from each other; and
Ar4 is a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.
2 . The heterocyclic compound of claim 1 , wherein the heterocyclic compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulae 1-1 to 1-3:
in Chemical Formulae 1-1 to 1-3,
R13 to R16 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; —P(═O)R101R102; —SiR101R102R103; and —NR101R102, or two or more groups adjacent to each other bond to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C60 heteroring, and R101, R102 and R103 are the same as or different from each other and each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group;
f is an integer of 0 to 5, and when f is 2 or greater, R13s are the same as or different from each other;
g is an integer of 0 to 3, and when g is 2 or greater, R14s are the same as or different from each other;
h is an integer of 0 to 6, and when h is 2 or greater, R15s are the same as or different from each other;
i is an integer of 0 to 2, and when i is 2 or greater, R16s are the same as or different from each other;
Ar1 has the same definition as in Chemical Formula 1; and
L1 to L3, Ar2, Ar3 and a to c have the same definitions as in Chemical Formula 2.
3 . The heterocyclic compound of claim 1 , wherein Ar4 is a substituted or unsubstituted C6 to C60 aryl group.
4 . The heterocyclic compound of claim 1 , wherein L1 to L3 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted C6 to C60 arylene group.
5 . The heterocyclic compound of claim 1 , wherein the heterocyclic compound represented by Chemical Formula 1 does not include deuterium as a substituent, or has a deuterium content of 1% to 100% with respect to a total number of hydrogen atoms and deuterium atoms.
6 . The heterocyclic compound of claim 1 , wherein the heterocyclic compound represented by Chemical Formula 1 is represented by any one of the following compounds:
7 . An organic light emitting device comprising:
a first electrode; a second electrode provided opposite to the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the one or more organic material layers comprise the heterocyclic compound of claim 1 .
8 . The organic light emitting device of claim 7 , wherein the organic material layer includes a hole transport layer, and the hole transport layer includes the heterocyclic compound.
9 . The organic light emitting device of claim 7 , wherein the organic material layer includes an electron blocking layer, and the electron blocking layer includes the heterocyclic compound.
10 . The organic light emitting device of claim 7 , wherein the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound.
11 . The organic light emitting device of claim 7 , wherein the organic material layer includes a light emitting layer, the light emitting layer includes a host material, and the host material includes the heterocyclic compound.
12 . The organic light emitting device of claim 7 , wherein the organic material layer further includes a heterocyclic compound represented by the following Chemical Formula 4:
in Chemical Formula 4,
R21 to R28 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; —P(═O)R201R202; —SiR201R202R203; the following Chemical Formula 5; the following Chemical Formula 6; and the following Chemical Formula 7, or two or more groups adjacent to each other bond to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C60 heteroring, and R201, R202 and R203 are the same as or different from each other and each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; and
any one of R21 to R28 is the following Chemical Formula 5, and another one is the following Chemical Formula 6; or the following Chemical Formula 7,
in Chemical Formulae 5 to 7,
L11 to L16 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group;
j is an integer of 0 to 5, and when j is 2 or greater, L11s are the same as or different from each other;
k is an integer of 0 to 5, and when k is 2 or greater, L12s are the same as or different from each other;
l is an integer of 0 to 5, and when 1 is 2 or greater, L13s are the same as or different from each other;
m is an integer of 0 to 5, and when m is 2 or greater, L14s are the same as or different from each other;
n is an integer of 0 to 5, and when n is 2 or greater, L15s are the same as or different from each other;
o is an integer of 0 to 5, and when o is 2 or greater, L16s are the same as or different from each other; and
Ar11 to Ar15 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.
13 . The organic light emitting device of claim 12 , wherein the heterocyclic compound represented by Chemical Formula 4 is represented by any one of the following Chemical Formulae 4-1 to 4-4:
in Chemical Formulae 4-1 to 4-4,
R31 to R34 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; —P(═O)R201R202; —SiR201R202R203; and —NR201R202, or two or more groups adjacent to each other bond to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C60 heteroring, and R201, R202 and R203 are the same as or different from each other and each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group;
p is an integer of 0 to 3, and when p is 2 or greater, R31s are the same as or different from each other;
q is an integer of 0 to 3, and when q is 2 or greater, R32s are the same as or different from each other;
r is an integer of 0 to 4, and when r is 2 or greater, R33s are the same as or different from each other;
s is an integer of 0 to 2, and when s is 2 or greater, R34s are the same as or different from each other;
L11, L12, Ar11, Ar12, j and k have the same definitions as in Chemical Formula 5;
L13, Ar13 and 1 have the same definitions as in Chemical Formula 6; and
L14 to L16, Ar14, Ar15, m, n and o have the same definitions as in Chemical Formula 7.
14 . The organic light emitting device of claim 12 , wherein the heterocyclic compound represented by Chemical Formula 4 does not include deuterium as a substituent, or has a deuterium content of 1% to 100% with respect to a total number of hydrogen atoms and deuterium atoms.
15 . The organic light emitting device of claim 12 , wherein the heterocyclic compound represented by Chemical Formula 4 is represented by any one of the following compounds:
16 . The organic light emitting device of claim 7 , further comprising one, or two or more layers selected from the group consisting of a light emitting layer, a light emitting auxiliary layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer and a hole blocking layer.
17 . A composition for an organic material layer, the composition comprising:
the heterocyclic compound represented by Chemical Formula 1 of claim 1 ; and a heterocyclic compound represented by the following Chemical Formula 4:
wherein, in Chemical Formula 4,
R21 to R28 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; deuterium; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; —P(═O)R201R202; —SiR201R202R203; the following Chemical Formula 5; the following Chemical Formula 6; and the following Chemical Formula 7, or two or more groups adjacent to each other bond to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C60 heteroring, and R201, R202 and R203 are the same as or different from each other and each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; and
any one of R21 to R28 is the following Chemical Formula 5, and another one is the following Chemical Formula 6; or the following Chemical Formula 7,
in Chemical Formulae 5 to 7,
L11 to L16 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group;
j is an integer of 0 to 5, and when j is 2 or greater, L11s are the same as or different from each other;
k is an integer of 0 to 5, and when k is 2 or greater, L12s are the same as or different from each other;
l is an integer of 0 to 5, and when 1 is 2 or greater, L13s are the same as or different from each other;
m is an integer of 0 to 5, and when m is 2 or greater, L14s are the same as or different from each other;
n is an integer of 0 to 5, and when n is 2 or greater, L15s are the same as or different from each other;
o is an integer of 0 to 5, and when o is 2 or greater, L16s are the same as or different from each other; and
Ar11 to Ar15 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.
18 . The composition of claim 17 , wherein the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 4 have a weight ratio of 1:9 to 9:1.Cited by (0)
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